Esters of ethylene glycol ethers



Patented Aug. 6, 1935 I 2,010,560

UNITED STATES PATENT OFFICE ESTEBS F ETHYLENE GLYCOL ETHEl tS Clayton Olin North, Nitro, W. Va" assignor, by mesneassignments, to Herbert S. Kreighbauin, Akron, Ohio No Drawing. Application October 22, 1932, Serial No. 639,043 r 2 Claims. (Cl. 260-106 This invention relates to .new compositions The a e e t s now'run to a Still designed containing oleates or other unsaturated fatty Vacuum distillation and distilled at a Pressure acid esters of ethylene glycol monomethyl ether. 1635 than 20 of y. M the n in One object of this invention is the provision of of the di ill i n. h d consisting of n 5 new plasticizers for nitrocellulose and resins, thylene glycol monomethyl ether and some oleic 5 such as phenol-formaldehyde resins. acid, are removed t0 temperature of pp x Another object of this invention is the provit ly C- at a p ssur f a ut 9 mm. The sion of new plasticizers having high boiling distillate is then run into a receiver for the ester. 4 points. The oleic acid ester of beta methoxy ethanol 10 A further object of this invention is the prodistills at about 220 C.-240 C. at 9 mm. pressure. 10 vision of a plasticizer having a, high resistance to This product is sufliciently pure for use as a plastiultra violet light. cizer for ultra-cellulose. However, if a purer Other objects of this invention will be in part material is desired, the product can be mixed with e i obvious and in part pointed out hereinafterabout five times its volume of hot water and- One example of myinvention is the oleic acid a base added until the water shows an alkaline ester of beta methoxy ethanol, which may be reaction. The ester is then separated from the called methoxyethyl oleate, whose structural aqueous portion and dried, preferably in vacuo,

formula may be represented; and vacuum distilled. The pure ester boils at about 222-225 C. at 6 mm. pressure.

, H n o l While I have given a specific example of my in- 20 vention, it is to be expressly understood that This ester may be prepared as follows: variations in the process may be employed. For Parts by weigh example, gaseous hydrochloric acid may be em- Ole1c acid 2256 io d as the condensing agent instead of sulfuric ylene glycol monomethyl other. and- 2 acid, in which case awater wash is not usually 25 Toluene 697 found to be necessary before distillation.

are charged into a suitable reaction vessel. A The heads of first fraction m in the on may be used in subsequent mixture of about 29 parts by weight of 66 B. vacuum distmati sulfuric acid and about 16 parts of water by estermcatmns after making anowanfies the weight are Stirred into the mixtureWhich 1s toluene, betamethoxy ethanol and oleic acid pres- 30 then heated so that slow distillation results. The reaction vessel is equipped with a column and The 1eate Ethan may be D wcondenser. Heating is carried on in such a way mum's:

that, beta methoxy ethanol (ethylene glycol. Pa ts by wei monomethyl ether) is largely r t n by t Beta butoxy ethanol 177 r flux from the column but the tciuen t r Oieic acid 288 and some methoxy ethanol go over int th n- Toluenen v86 denser. By means of a separator, the toluene Sulfuric acid v(66 B.) dissolved-in equal distilled out is continuously removed from the weight of water 3.6 water layer and returned to the esteriflcation are reacted in apparatus y the od vessel. The heat necessary for promoting the scribed above under the P p n f me h xyreaction and removing" water maybe supplied in ethyl olelte- This Product ethyl oleate, any convenient manner, for example, by circulatdistllls between D 6 a a u 12 m ing oil or steam. Stirring during esteriflcation p ssure- The mate a i a pa y l w a d isv desirable but not necessary. The esterificalightly vi l q d. tion, which is quite rapid, requires-from about The oleates of diethylene G y t sm y also 4 to 5 hours for completion. I be employed. For example, the oleate of diethy- When water ceases to come on, the distillation iene glycol mon u yl oth m y be p epare as is continued and most of the toluene and follows:

"* methoxy ethanol are removed at atmospheric Parts by weight pressure, to a vapor temperature of about 104 "Diethyien'e glycol mono butyl ether 243 to 105 C. The crude reaction product is then Oleicacid 282 washed with about an equal volume of water. Toluen 86 The wash mixture is allowed to settle and the 66 Sulfuric acid (dissolvedinanequal weight 36 I0 aqueous layer is drawn off. of water) are reacted by the same method and in similar apparatus as described under the preparation of methoxy ethyl oleate. In this case the esterification takes somewhat longer. Usually in six hours all the water to be liberated has been collected. In all these esterifications the reaction is carried on until the theoretical amount of water is collected. The product distills between 255 and 270 C. at 10 mm. The oleate of diethylene glycol mono butyl ether has a density of about 0.905 at 25 C.

The methods herein described for the preparation of the ether alcohol oleates are to be considered as illustrative only of how these products may be prepared. I do not limit myself to these monly known among rubber-men as ponti resin.

The term radical" as used above includes the meaning of the word rest" as understood in German technology.

What I claim is:

1. As a new compound, the oleic acid ester of beta methoxy ethanol.

2. A composition adapted for use as a plasticizer and a solvent for nitrocellulose and resins, which consists of an oleic acid ester of a methoxy ethanol.

CLAYTON OLIN NORTH. 

